Sodium Carbonate → HCID 10901505, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred cooled solution of 1-[5-Fluoro-2-(methylthio)phenyl]-2-(pyrrol-1-yl)ethanone (22c) (1.76 g, 7.06 mmol) in dichloromethane (12 ml) was added dropwise in 30 minutes a solution of m-chloroperbenzoic acid (71.5% grade, 1.70 g, 7.06 mmol) in dichloromethane (10 ml). After stirring for 45 minutes at 0° C., the mixture was treated with a 5% solution of sodium carbonate in water (41 ml) and was stirred for 15 minutes at room temperature. The organic phase was separated and water was extracted with dichloromethane (3×10 ml). The organic layers were dried and evaporated, the residue was chromatographed (10% dichloromethane in ethyl acetate) to afford 1.02 g of 23c as white crystals that darkened rapidly (64% yield). 1H NMR (CDCl3) δ8.42-8.35 (m, 1H); 7.61-7.51 (m, 2H); 6.68-6.62 (m, 2H); 6.26-6.24 (m, 2H); 5.41-5.17 (q, 2H, J=31.32, 17.87 Hz); 2.77 (s, 3H).

Provenance & Evidence